ES2279173T3 - FUNGICIDE BLENDS FOR THE FIGHT OF RICE PATHOGENS. - Google Patents

Abstract

Fungicidal mixtures for controlling rice pathogens, comprising, as active componen

Description

Fungal mixtures for pathogen control of rice.

The present invention relates to mixtures fungicides for the combat of rice pathogens, which contain as active components

1) the compound of the formula I

one

Y

2) the compound of formula II

2

in an effective amount so synergistic

The invention further relates to a procedure for combating rice pathogens with mixtures of compound I with compound II, and the use of compound I with the compound II for obtaining such mixtures, as well as agents They contain these mixtures.

The compound of the formula I, 2- [2- (2,3-bis-methoxyimino-1-methyl-butylidenaminooxymethyl) -phenyl] -2-methoxyimino-N-methyl-acetamide, belongs to the class of active strobilurin products, whose obtaining and its action against harmful fungi, especially against Rice diseases are known (WO 97/15552; common name: orisastrobin).

Compound II, 5-Chloro-7- (4-methyl-piperidin-1-yl) -6- (2,4,6-trifluor-phenyl) - [1,2,4] triazolo [1,5-a] pyrimidine, its obtaining and its action against harmful fungi, are also known from the literature (WO 98/46607).

Orisastrobin mixtures with other products assets are known from (WO 99/48366, WO 99/48367).

Mixtures of triazolopyrimidines with various active products are generally known by the EP-A 988 790. Mixtures with derivatives of Synthetic strobirulin are included in the manifestation general.

The synergistic mixtures of derivatives of triazolopyrimidine known from EP-A 988 790 se they use as products with fungicidal efficacy against various diseases of cereals, vegetables and vegetables, especially mildew in wheat and barley, or gray mold in apples.

The US 5,593,996 shows the effectiveness of triazolopyrimidine derivatives, as used in EP-A 988 790, against Pyricularia oryzae.

US 6 268 371 describes synergistic mixtures of triazolopyrimidines known from US 5 593 996 with the phenoxyanil amide fungicide, especially for the combat of rice pathogenic Pyricularia and Rhizoctonia types.

Due to special growing conditions of rice plants there are requirements in a rice fungicide clearly different from those raised in fungicides that apply in cultivation of cereals or fruits. In the application method there are aggravating differences: in rice crops, the fungicide is routinely distributes directly to the soil, during, or Shortly after planting. The fungicide is absorbed in plants at through the roots, and the plant parts are transported to protect in the sap of the plant. Therefore, for fungicides of Rice is essential a high systemic power. On the contrary, in cultivation of cereals or fruits, the fungicide is usually applied on the leaves or fruits, therefore, in these crops the systemic power of active products plays a role considerably lower.

In rice they are also typical pathogens different from those usual in cereals or fruit. Pyricularia oryzae and Corticium sasakii (syn. Rhizoctonia solani / AG 1-IA) are the pathogens of widespread rice plant diseases in most cases. These are not produced in scope worthy of mention in other crop plants. Rhizoctonia solani is the only significant pathogen in agriculture within the Agaricomycetidae subclass . In contrast to most different fungi, this fungus does not attack the plant through spores, but through a micellar infection.

For these reasons, the results regarding fungicidal activity of active products in cereal cultivation or Fruits are not transferable to rice crops.

Orisastrobin is known as fungicide of special rice. Regarding a more effective pathogen control of rice with application quantities as small as possible, the This invention was based on mixtures of orisastrobin which will show an improved action against harmful fungi with quantity reduced total of active products distributed.

Therefore the combination of active products defined at the beginning. It was also discovered that, with simultaneous joint application or separation of compounds I, and of compounds II, or in the case of application of compounds I and of Compounds II successively, you can fight harmful fungi better than isolated compounds.

In the preparation of the mixtures it is used preferably pure active products I and II, to which you can add, if necessary, other active ingredients against harmful fungi or other parasites, such as insects, arachnids or nematodes, or also herbicidal active ingredients or regulators of growth, or fertilizers.

Mixtures of compounds I and II, or the simultaneous or common use of compounds I and II, distinguished by an extraordinary action against harmful fungi of the class of ascomycetes, deuteromycetes and basidiomycetes. Partly they have systemic efficacy, and can therefore be used also as insecticides for leaves and soil.

These have a special meaning for combating harmful fungi in rice plants and in their seeds, such as Bipolaris and Drechslera types. They can be used especially advantageously for the combat of Pyricularia oryzae , the cause of rice rust, and the disease of leaf sheaths in rice, caused by Corticium sasakii (syn. Rhizoctonia solani ).

Compounds I and compound II can be apply simultaneously together or separately, or successively, not generally having an impact on success of combat the order in the case of separate application.

Compounds I and the compound II in a weight ratio of 100: 1 to 1: 100, preferably 20: 1 to 1:50, especially 5: 1 to 1:20.

The quantities of application of the mixtures according to the invention they are generally located, according to the type of compound and of desired effect, at 5 g / ha at 2000 g / ha, preferably 50 g / ha at 1500 g / ha, especially 50 to 750 g / ha.

Correspondingly, the amounts of application for compound I is generally 1 to 1000 g / ha, preferably 10 to 750 g / ha, especially 20 to 500 g / ha.

Correspondingly, the amounts of application for compound II is generally 1 to 1000 g / ha, preferably 10 to 750 g / ha, especially 20 to 500 g / ha.

In the case of seed treatment they are used in general, mixture application amounts of 0.001 to 1 g / kg of seeds, preferably 0.01 to 0.5 g / kg, especially 0.01 to 0.1 g / kg

In the fight of harmful pathogenic fungi for plants, the separate or common application of compounds I and II, or of the mixtures of compounds I and II, it is carried out by spraying or sprinkling seeds, plants, or soils, before or after planting of plants, or before or after plant growth In the case of application against rice pathogens, the application of compounds is carried out jointly or separately, preferably by application of granulated or ground sprays.

The mixtures according to the invention, or the compounds I and II, can be transformed into the formulations common, for example, solutions, emulsions, suspensions, dusting agents, powders, pastes and granules. The way of application conforms to the respective purpose of employment; in any case, it must ensure the finest and most uniform distribution of the compound according to the invention.

The formulations are obtained in a known way itself, for example by dilution of the active product with solvents and / or support substances, if desired under the use of emulsifying and dispersing agents. As solvents / substances auxiliary, for this purpose they essentially take into account:

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        water, aromatic solvents (for example Solvesso products, xylene), paraffins (eg oil fractions), alcohols (e.g. methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, dimethyl fatty acid amides, fatty acids and acid esters fatty In principle, mixtures of solvents,

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        supporting substances, such as natural milled minerals (for example kaolins, aluminum oxides, talc, crete) and minerals synthetic milled (for example highly silicic acid dispersed, silicates); emulsifying agents, such as non-emulsifying agents ionogens and anionics (for example ether of polyoxyethylene fatty alcohol, alkyl sulfonates and arylsulfonates), and dispersing agents, such as leaching sulphites of lignin and methylcellulose.

As surfactants, the alkaline, alkaline earth, ammonium salts of ligninsulfonic acid, naphthalene sulfonic acid, phenolsulfonic acid, acid dibutylnaphthalene sulfonic, alkylarylsulfonates, alkylsulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and glycol ethers of sulfated fatty alcohols, in addition to condensation products of sulfonated naphthalene and derivatives of naphthalene with formaldehyde, naphthalene condensation products, or of naphthalene sulfonic acids with phenol and formaldehyde, polyoxyethylenectylphenol ether, isooctylphenol, octylphenol, nonylphenol ethoxylated, alkyl phenol polyglycol ether, polyglycol ether of tributhenyl, polyglycol ether of triesterylphenyl, rentyl polyether alcohols, alcohol and alcohol condensates fatty ethylene oxide, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, ether acetate polyglycol of lauric alcohol, sorbitol esters, leaching sulphites of lignin, or methylcellulose.

To obtain sprayable solutions directly, emulsions, pastes or oil dispersions, enter under consideration boiling point mineral oil fractions medium to high, such as kerosene or diesel oil, in addition to oils of tar, as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example benzene, toluene, xylene, paraffin, tetrahydronaphthalene, naphthalene alkylated or derivatives thereof, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, for example dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone or water.

Powder agents can be obtained from dispersion and sprinkling by mixing or grinding set of the active substances with a solid support substance.

The granules, for example granules of coating, impregnated and homogeneous, can be obtained by binding of active products to solid support substances. The solid support substances are, for example, mineral earth, such as silica gel, silicates, talc, kaolin, attaclay, limestone, lime, Crete, bowl, loess, clay, dolomite, diatomaceous earth, sulfate of calcium and magnesium, magnesium oxide, synthetic materials milled, fertilizing agents, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and plant products, such as cereal flour, tree bark flour, wood and husks of walnut, cellulose powder, or other solid support substances.

The formulations generally contain between a 0.01 and 95% by weight, preferably between 0.1 to 90% by weight of active products. In this case, the active products are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

Examples of formulations are: 1. Products for the dilution in water.

A) Water-soluble concentrates (SL)

10 parts by weight of products are dissolved active in water, or in a water-soluble solvent. Alternatively wetting agents or other auxiliary agents are added. In the dilution in water dissolves the active product.

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B) Dispersible concentrates (DC)

20 parts by weight of products are dissolved active in cyclohexanone under the addition of a dispersing agent, by example polyvinylpyrrolidone. In the case of dilution in water, It produces a dispersion.

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C) Emulsifiable concentrates (EC)

15 parts by weight of products are dissolved active in xylene under the addition of Ca dodecylbenzenesulfonate and castor oil ethoxylate (respectively 5%). In the case of dilution in water produces an emulsion.

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D) Emulsions (EW, EO)

40 parts by weight of products are dissolved active in xylene under the addition of Ca dodecylbenzenesulfonate and castor oil ethoxylate (respectively 5%). This mixture is introduced into water by means of an emulsifying machine (Ultraturax), and it becomes a homogeneous emulsion. If Dilution in water produces an emulsion.

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E) Suspensions (SC, OD)

20 parts by weight of products crumble active, with the addition of dispersing and wetting agents and water, or an organic solvent, in a ball mill with mechanism stirrer to give a fine suspension of active products. At In case of dilution in water, a stable suspension of active product.

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F) Water dispersible and water-soluble granules (WG, SG)

50 parts by weight of finely ground active products under the addition of dispersing agents and humectants, and are obtained as water dispersible granules or water-soluble by means of technical devices (for example extrusion, spray tower, fluidized bed). In the case of dilution in water produces a stable dispersion or dissolution of product active.

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G) Water dispersible and water-soluble powders (WP, SP)

75 parts by weight of products are milled active under the addition of dispersing and wetting agents, as well as silicic acid gel, in a rotor-strator mill. In the case of dilution in water a dispersion or stable solution of active product.

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2. Products for direct application.

H) Powders (DP)

5 parts by weight of finely ground active products, and mix intimately with 95% kaolin finely divided. In this way an agent of sprinkle.

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I) Granules (GR, FG, GG, MG)

0.5 parts by weight of finely ground active products, and bind with 95.5% of support substance. In In this case, the commonly used procedures are extrusion, the spray drying or fluidized bed. In this way get a granulate for direct application.

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J) ULV Solutions (UL)

10 parts by weight of products are dissolved active in an organic solvent, for example xylene. In this way a product is obtained for direct application.

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The active ingredients can be used as such, in the form of its formulations, or the forms of application already prepared, for example in the form of sprayable solutions directly, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusting agents, dispersion, granules, by spraying, fogging, sprinkling, dispersion or irrigation. The application forms are adjusted completely for the purpose of employment; in any case, these should ensure the finest possible distribution of the principles active according to the invention.

Application forms can be prepared for from emulsion concentrates, pastes or wettable powders (wettable spray powder, oil dispersions), by adding water. To obtain emulsions, pastes or oil dispersions can be homogenized in water substances as such, or dissolved in an oil or solvent, by medium of wetting, adherent, dispersing agents or emulsifiers But you can also get concentrates consisting of active substance, wetting agent, adherent, dispersant or emulsifier, and eventually solvent or oil, which They are suitable for dilution with water.

The concentrations of active substance in ready-made preparations can be varied in larger intervals. These are generally between 0.0001 and 10%, preferably between 0.01 and 1%.

The active ingredients can also be used with good result in the procedure of Ultra-Low-Volume (ULV), being possible to distribute formulations with more than 95% by weight of active substance, or even the active substance without additions.

To the active ingredients can be added oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticidal agents, bactericides, in case also just immediately before application (tank mix). You can add these agents to the agents according to the invention in weight ratio 1:10 to 10: 1.

Compounds I and II, either mixtures, or corresponding formulations are applied by treating the fungi harmful, plants, seeds, soils, surfaces, materials or spaces to preserve them, with an effective amount such as mixing fungicide, or of compounds I and II, in the case of separate dispersion The application can be done before or after of attack due to harmful fungi.

The fungicidal action of the compound and the Mixtures can be shown by the following tests.

Active products were made separately or together as a stock solution with 0.25% by weight of active product in acetone or DMSO. To this solution 1% was added by weight of emulsifier Uniperol® EL (wetting agent with action emulsifier and dispersant based on ethoxylated alkylphenols), and diluted with water corresponding to the desired concentration.

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Example of application

Effectiveness against rice rust caused by Pyricularia oryzae

Leaves of rice shoots of the "Tai-Nong 67" species were sprayed drip with aqueous suspension at the concentration of active product indicated above. The next day the plants were inoculated with an aqueous spore suspension of Pyricularia oryzae . The test plants were then placed in heated chambers at 22-24 ° C and 95-99% relative humidity for 6 days. Then the extent of attack development on the leaves was determined visually.

The valuation is carried out by determination of the attacked leaf surfaces in percentage. This values Percentages became degrees of action.

The degree of action (W) is calculated according to the Abbot's formula as follows:

W = (1 - \ alpha / \ beta) \ cdot 100

α

corresponds to the fungal attack of the plants treated in%, and

\beta

corresponds to the fungal attack of the (control) plants not treated in%.

In the case of an action grade of 0, the attack of the treated plants corresponds to that of the control plants not treated; in the case of an action grade of 100, the plants Treated have no attack.

The degrees of action to be expected from mixtures of Active products are determined according to Colby's formula [R. S. Colby, Weeds 15, 20-22, (1967)], and are compared with the degrees of action observed.

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Colby formula:

E = x + y - x \ cdot y / 100

AND

degree of action to be expected, expressed in% control untreated, in the case of using the mixture constituted by active products A and B in concentrations a and b,

x

the degree of action, expressed in% of control not treated, in the case of use of active product A in the concentration to,

Y

the degree of action, expressed in% of control not treated, in the case of use of active product B in the concentration b.

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The comparative compounds used were mixtures of known compounds A and B described in the EP-A 988 790:

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3

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TABLE A Isolated active products

4

TABLE B Mixtures according to the invention

5

TABLE C Comparative tests - mixtures with compounds A and B proposed in EP-A 988 790 for mixtures with strobirulin derivatives

6

From the test results it follows that mixtures of orisastrobin with the derivative of triazolopyrimidine II according to the invention show an efficacy clearly higher, while, in the case of quantities of comparable application, mixtures with compounds A and B proposed in EP-A 988 790 are just slightly active at most.

Claims (10)

1. Fungicidal mixtures containing as active components 1) the compound of the formula I 7 Y 2) the compound of formula II 8 in an effective amount so synergistic 2. Fungicidal mixtures according to claim 1, containing the compound of the formula I and the compound of the formula II in a weight ratio of 100: 1 to 1: 100. 3. Fungicidal agent containing a substance liquid or solid support, and a mixture according to claim 1 or 2. 4. Procedure for combating harmful rice pathogenic fungi, characterized in that the fungi, their living space, or the plants, soils or seeds to be preserved from fungal attack are treated, with an effective amount of compound I and compound II according to claim 1, in synergistically effective amounts. 5. Method according to claim 4, characterized in that the compounds I and II according to claim 1 are distributed simultaneously, and precisely jointly or separately, or successively. Method according to claim 4, characterized in that the mixture according to claims 1 or 2 is applied in an amount of 5 g / ha at 2,000 g / ha. Method according to claims 4 and 5, characterized in that the mixture according to claims 1 or 2 is applied in an amount of 0.001 to 1 g / kg of seeds. 8. Method according to claims 4 to 7, characterized in that the harmful fungus Pyricularia oryzae is combated. 9. Seeds containing the mixture according to claims 1 or 2 in an amount of 0.001 to 1 g / kg. 10. Use of compound I and compound II according to claim 1, for obtaining an appropriate agent for the combat of harmful rice pathogenic fungi.